CN103805211A - Liquid crystal composition for multiple modes and application thereof - Google Patents
Liquid crystal composition for multiple modes and application thereof Download PDFInfo
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- CN103805211A CN103805211A CN201410040239.1A CN201410040239A CN103805211A CN 103805211 A CN103805211 A CN 103805211A CN 201410040239 A CN201410040239 A CN 201410040239A CN 103805211 A CN103805211 A CN 103805211A
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Abstract
The invention provides a liquid crystal composition. The liquid crystal composition comprises the following components by weight percentage: 1, a first component comprises compounds which are represented by a general formula I and a general formula II, the content of the first component is 1-65%, and preferentially is 35-65%; 2, a second component comprises compounds which are represented by a general formula III, a general formula IV and a general formula V, the content of the second component is 1-60%, and preferentially is 30-60%; and 3, a third component comprises compounds which are represented by a general formula VI and a general formula VII, the content of the third component is 1-55%, and preferentially is 5-35%. The liquid crystal composition has the characteristics of fast response time, low rotary viscosity, high-definition bright spot, high dielectric anisotropy and high transmittance and can well meet the rigorous requirements of a shutter mirror and display devices such as 3D (three dimension), TN (twisted nematic), STN (super twisted nematic), TN-TFT(twisted nematic-thin film transistor), OCB (optically compensated birefringence), IPS (in-plane switching), PS-IPS (-in-plane switching), VA-IPS (vertical alignment-in-plane switching), FFS (fringe field switching), PS-FFS (-fringe field switching), PS-VA-IPS (polymer stabilized-vertical alignment-in-plane switching) and the like.
Description
Technical field
The invention belongs to liquid crystal material field, be specifically related to a kind of liquid-crystal composition that can be used for various modes.
Background technology
The fundamental research of liquid crystal essential property, basic theories aspect starts early, liquid crystal material is used for technique of display as far back as nineteen sixty-eight, the Heilmeier of Princeton institute of RCA Corp. of the U.S. etc. has invented the liquid-crystal display that utilizes liquid crystal dynamic scattering (Dynamic Scattering, DS) pattern.M.Schadt in 1971 etc. deliver liquid crystal twisted-nematic effect (Twisted Nematic, TN); The same year, M.Schiekel etc. almost delivered electro-optic birefringent effect (Electrically Controlled Birefringence, ECB) pattern with M.Hareng etc. simultaneously.In succession find subsequently the effects such as host and guest (Guest Host, GH) effect, phase transformation (Phase Chang, PC) effect, super twisted nematic (Super TN).Initial business-like liquid-crystal display mostly is TN or STN type, this class display is in increased in size and pixel rear drive difficulty, until nineteen eighty-three adopts active matrix (the Active Matrix of P.Brody proposition, AM) prospect of thin film transistor (Thin Film Transistor, TFT) type of drive liquid-crystal display is just clear bright and clear gradually.
The 80s and 90s in 20th century is the high-speed developing period of TFT liquid-crystal display, and American-European countries and Japanese manufacturer have successively carried out relevant exploitation, until manufacturer of late nineteen eighties Japan just grasps main production technology completely and carries out scale operation.A large amount of uses of TFT-LCD are from notebook computer, and along with the continuous increase of PC demand, TFT-LCD has become the main flow of liquid-crystal display.
The development of TFT-LCD TV has entered the epoch of a large size, wide visual angle, fast-response, TN+Film, coplanar conversion (In Plane Switching, IPS) and fringing field switch (Fringe Field Switching, FFS) the wide visual angle that technology approaches 180o with it receives much concern always, and for example, along with expansion (outdoor application, high and low temperature environment, the high definition of Application Areas and scope, the more long lifetime), prior art will meet these application and seem very difficult.Technician in industry is also making great efforts to address these problems always, all carrying out technological innovation from the making technology of indicating meter to assembling and each starting material, liquid crystal material more needs to have breakthrough progress to adapt to the requirement under new condition as the core material of liquid-crystal display.
The development of lcd technology and Application Areas is more also had higher requirement to liquid crystal material, and these requirements have: good chemistry and thermostability, to the good stability of electric field and electromagnetic radiation; Lower viscosity is to reach low voltage and fast-response; Wider nematic temperature range is normally worked under the environment above and below room temperature; Larger dielectric anisotropy, reduces driving voltage.Show for TFT, the requirement of liquid-crystal composition is higher, needs high initial electrical resistivity, and resistivity little increase to the greatest extent after heating and/or after UV exposure; There is not crystallization and/or smectic phase even if require at (20 ℃ or lower) at low temperatures; The velocity of variation of viscosity with temperature is as far as possible little; Degree of birefringence is larger, adapts to thinner display design; Higher transmitance, to reach better contrast gradient and in bright gay color.
It is very difficult that the liquid-crystal composition obtaining from existing technology will be realized these parameters simultaneously, the present invention's object is to provide the shutter glasses for this generic request harshness, in 3D and TN, STN, TN-TFT, OCB, IPS, PS-IPS, VA-IPS, FFS, PS-FFS and PS-VA-IPS display device, its energy is fine or meet preferably the requirement of these indicating meters to liquid-crystal composition, and preferably has the composition of fast response time, low rotary viscosity, high clearing point, high dielectric anisotropy and high permeability.
Summary of the invention
For the weak point of art technology, the object of the invention is to propose a kind of liquid-crystal composition that can be used for various modes.
Another object of the present invention is the application that proposes described liquid-crystal composition.
The concrete technical scheme that realizes above-mentioned purpose of the present invention is:
A liquid-crystal composition that can be used for various modes, is characterized in that, the component that comprises following weight percent:
The compound that (1) first component comprises formula I and general formula II representative, its content is 1-65%, preferably 35-65%;
(2) compound that second component comprises general formula III, general formula IV and general formula V representative, its content is 1-60%, preferably 30-60%;
The compound that (3) the 3rd components comprise general formula VI and general formula VII representative, its content is 1-55%, preferably 5-35%;
Wherein R
1, R
2, R
3independently represent separately H, methyl or C
2-C
12the alkyl or alkenyl of atom, described C
2-C
12the alkyl or alkenyl of atom be unsubstituted, by CN or CF
3mono-substituted or mono-substituted by halogen, described C
2-C
12one or more CH in the alkyl or alkenyl of atom
2group can by-O-,-S-, ,-C ≡ C-,-CF
2o-,-OCF
2-,-OC-O-,-O-CO-with O atom not each other the mode of Direct Bonding replace;
L
1, L
2represent independently of one another H or F, L
3, L
4, L
5, L
6represent independently of one another H, F, Cl, CF
3, CHF
2in one;
Ring A and ring B independently represent separately
in one;
Ring C and ring D are from independently representing
in one,
Z
1represent singly-bound ,-CH
2cH
2-,
-CH=CH-,-C ≡ C-,-CF
2o-,-OCF
2-,-CH
2o-,-OCH
2-,-COO-,-OCO-,-C
2f
4-,-CF=CF-,-CH=CHCH
2one in O-,
Z
2represent singly-bound or-C
2h
4-,
Z
3and Z
4represent independently of one another singly-bound or
-CH
2o-,-C
2h
4-;
L, m, n, p, r and s represent 0 or 1 independently of one another;
Wherein, R
4, R
5, R
6and R
7represent independently of one another C
1-C
5alkyl or C
2-C
5thiazolinyl, wherein R
4, R
5in one or more-CH
2-can be replaced by-O-;
L
7, L
8, L
9, L
10and L
11represent independently of one another H atom or F atom;
X and Y represent F atom, OCF independently of one another
3, OCF
2-CF=CF
2, OCHF
2and C
1-C
5alkyl in one;
Described general formula VI is one or more in five kinds of structures shown in formula VI A-VI E:
Wherein, R
8and R
9represent independently of one another C
1-C
5alkyl; L
12, L
13and L
14represent independently of one another H or F atom; W and Q independently represent F atom, OCF separately
3, OCF
2-CF=CF
2and C
1-C
5alkyl in one.
Preferably, the component that described liquid-crystal composition comprises following weight percent:
The compound that (1) first component comprises formula I and general formula II representative, its content is 35-65%, its formula of II compound >=5%; (2) compound that second component comprises general formula III, general formula IV and general formula V representative, its content is 30-60%, its formula of III >=15%; The compound that (3) the 3rd components comprise general formula VI and general formula VII representative, its content is 5-35%, its formula of VII≤15%.
More preferably, the component that described liquid-crystal composition comprises following weight percent:
The compound that (1) first component comprises formula I and general formula II representative, its content is 35-65%, its formula of II >=10%; (2) compound that second component comprises general formula III, general formula IV and general formula V representative, its formula of III is 15-35%, and general formula IV is 5-20%, and general formula V is 5-20%; The compound that (3) the 3rd components comprise general formula VI and general formula VII representative, its formula of VI is 6-20%, general formula VII is 0-15%.
The mixture that experimental results show that the compound that comprises generalformulaⅰcompound and at least one II A or II B has lower rotary viscosity and the relatively nematic phase of wide temperature range, larger specific inductivity and high transmissivity.They can be used as the chief component of liquid-crystal composition, then coordinate the compound of general formula III-general formula VII, can mix the composition that is applicable to multiple use display format, and therefore its feature is applicable to mobil phone, TV, PC, video monitor etc.
Wherein, described compound of Formula I is preferably one or more in compound shown in following structure:
Described I compounds, can adopt the one in following three kinds of preparation methods prepare and obtain:
Preparation method one:
(1) alkyl phenyl-3-3 ', 5 '-trifluoro-biphenyl carries out low temperature butyllithium with difluorodibromomethane and reacts, and obtains compound 1;
(2) compound 1 and the fluoro-4-benzyloxy of 3,5-bis-phenol reactant, obtain compound 2;
(3), take palladium carbon as catalyzer, compound 2 and hydrogen reaction, obtain compound 3;
(4) compound 3 reacts with five fluorine propylene sulfonic acid fluoride, obtains target compound.
Preparation method two:
(1) alkyl pyrans-2, the grignard reagent that 6-difluorobenzene monobromomethane and reactive magnesium generate, with the reaction of 3,5-difluorobenzonilyile, obtains 1 of compound (method two);
(2) under potassium tert.-butoxide alkaline condition, compound 1 reacts with methyl triphenyl phosphonium iodide, and products therefrom nitrile palladium carbon shortening, obtains 2 of compound (method two);
(3) compound 2, after the reaction of low temperature butyllithium, reacts with trimethyl borate, obtains 3 of compound (method two);
(4) compound 3, through hydrogen peroxide oxidation, obtains 4 of compound (method two);
(5), take 1.3-dimethyl 2-imidazolidone as solvent, under the alkaline condition of triethylamine, compound 4 reacts with five fluorine propylene sulfonic acid fluoride, obtains 5 of target compound (method two).
Preparation method three:
(1) with tosic acid and 2,6-toluene di-tert-butyl phenol for dewatering agent, propyl group propylene glycol and the reaction of 3,5-difluorobenzaldehyde, obtain 1 of compound (method three);
(2) compound 1, after the reaction of low temperature butyllithium, reacts with difluorodibromomethane, obtains 2 of compound (method three);
(3) compound 2 and 3,5-difluoro benzyloxy phenol reactant, obtain 3 of compound (method three);
(4) compound 3, through palladium carbon shortening, is sloughed benzyloxy, obtains 4 of compound (method three);
(5), under the alkaline condition of triethylamine, compound 4 reacts with five fluorine propylene sulfonic acid fluoride, obtains 5 of target compound (method three).
Described general formula II compound is one or more in compound shown in following structure:
Preferably, in general formula III, R
4, R
5represent C
2-C
5alkyl, C
2-C
5thiazolinyl or C
1-C
5alkoxyl group, and R
4, R
5in have one at least for alkyl, be selected from the one in following minor:
Wherein, alkyl, thiazolinyl and alkoxyl group all represent C independently of one another
2-C
5alkyl, C
2-C
5thiazolinyl, C
1-C
5alkoxyl group; In formula III B, the alkyl on both sides can be identical or different.
The compound of general formula III representative is preferably one or more in following structure representative compound:
The compound of described general formula I V representative below three minors represents:
Wherein, the compound of described general formula I V representative is preferably one or more in following structure representative compound:
Wherein, the compound of described general formula V representative can following minor represent:
Wherein, R
7represent independently of one another C
2-C
5alkyl, Y represents F atom, OCF independently of one another
2-CF=CF
2and C
2～C
5alkyl.
The compound of described general formula V representative is preferably one or more in compound described in following structure:
The compound of described general formula VI and general formula VII representative can be expressed as structure:
Wherein, R
8and R
9represent independently of one another C
1-C
5alkyl; L
12, L
13and L
14represent independently of one another H atom or F atom; W and Q independently represent F atom, OCF separately
3, OCF
2-CF=CF
2and C
1-C
5alkyl in one.
The compound of general formula VI representative is preferably one or more in following structure representative compound:
Wherein, one or more in the following structure representative of the compound compound of described general formula VII representative:
The application of liquid-crystal composition of the present invention in shutter glasses, 3D and TN, STN, TN-TFT, OCB, IPS, PS-IPS, VA-IPS, FFS, PS-FFS and PS-VA-IPS mode display part.
The preparation method of liquid-crystal composition of the present invention is without particular restriction, can adopt ordinary method that two or more compound are produced, as the method preparation by high temperature mixing different components and dissolve each other, or liquid-crystal composition is dissolved in to solvent the mixing for this compound, then under reduced pressure distills out this solvent.
Beneficial effect of the present invention is:
In liquid-crystal composition provided by the present invention, the compound of general formula I representative has moderate optical anisotropy, high dielectric anisotropy, and mutual solubility is good, excellent combination property.
The negative dielectric anisotropic component of II class general formula representative provided by the present invention, has good mutual solubility, and the compound of itself and general formula I representative is as the chief component of liquid-crystal composition.They have lower viscosity, make the liquid crystal response time can be not oversize; There is higher clearing point, be adapted at using in wide temperature range; There is higher transmitance, improved contrast gradient and the brightness of liquid-crystal display, improved the sharpness of display frame; So general formula I and general formula I I have the application of relative broad range.In order to coordinate the application of different field liquid-crystal display, need to allocate the liquid-crystal composition of different parameters, so can also add on this basis general formula III-VII class liquid crystal to reach concrete parameter request.
The compound of III class general formula representative provided by the present invention is two Isosorbide-5-Nitrae-cyclohexane structures, and this structure has low viscosity, and low melting point performance has been improved the low-temperature performance of composition, and the nematic phase low temperature range of composition is expanded.The compound of general formula I V provided by the present invention and V class representative is tricyclic structure, and wherein general formula I V contains two Isosorbide-5-Nitrae-hexanaphthenes and an Isosorbide-5-Nitrae-phenylene; General formula V contains an Isosorbide-5-Nitrae-hexanaphthene and two Isosorbide-5-Nitrae-phenylenes.This two class formations mutual solubility is good, and optical anisotropy and dielectric anisotropy are moderate, also have certain clearing point, and viscosity is also little, is suitable as the component that regulates parameter.
General formula VI compounds provided by the present invention is Fourth Ring structure, has large optical anisotropy and high clearing point performance, has unusual effect for the clearing point and the optical anisotropy that promote composition.In addition, end is that the VI compounds of polar group (replacement of F atom) also has higher dielectric anisotropy.General formula VII compounds provided by the present invention is terphenyl structure, and its optical anisotropy is larger, and dielectric anisotropy and clearing point are moderate, applies more in the lower reality of the thick requirement of some box.
The liquid-crystal composition that the present invention proposes is for requiring harsh shutter glasses, in 3D and TN, STN, TN-TFT, OCB, IPS, PS-IPS, VA-IPS, FFS, PS-FFS and PS-VA-IPS display device, can be fine or meet preferably the requirement of these indicating meters to liquid-crystal composition.
Accompanying drawing explanation
Fig. 1 is optical throughput-voltage-contrast curve of embodiment 1 and comparative example 1.
Fig. 2 is optical throughput-voltage-contrast curve of embodiment 10 and comparative example 2.
Embodiment
Following examples are used for illustrating the present invention, but are not used for limiting the scope of the invention.
Except as otherwise noted, in context, per-cent is mass percent, and all temperature are degree Celsius to provide.Use following abbreviation: c.p=clearing point, △ n is optical anisotropy,
for specific refractory power (589nm, 20 ℃).η (mm
2/ s, 20 ℃) be volume viscosity.Δ ε is dielectric constant anisotropy (20 ℃, 1000Hz).The character voltage of V10 threshold voltage=in the time that relatively transmitance changes 10% (V, 25 ℃), the character voltage of V90 saturation voltage=in the time that transmitance changes 90% relatively (V, 25 ℃).Ton is until the time while connecting while reaching maximum countrast 90%, and toff is until the time while cutting off while reaching maximum countrast 10%, and τ is the ton+toff(time of response) (ms).Except as otherwise noted, all optical datas are all measured at 20 ℃.
For the ease of representing, in following examples, formula I-VII compound represents with sequence number hereinbefore, wherein alkyl and alkyl oxide numeral in formula I and general formula II, and example is as follows:
sequence number is II-28, wherein R
2for butyl and R
3during for ethyl, be expressed as 4-II-28-2, R
2for butyl ether and R
3during for ethyl, be expressed as 4O-II-28-2.
Embodiment 1:
The proportioning of the liquid-crystal composition of table 1 embodiment 1 and performance perameter
In table 1, compound 2-I a-17 synthetic route is as follows:
Feed change, can synthesize other I compounds equally.
The proportioning of the liquid-crystal composition of table 2 embodiment 2 and performance perameter
The proportioning of the liquid-crystal composition of table 3 embodiment 3 and performance perameter
The proportioning of the liquid-crystal composition of table 4 embodiment 4 and performance perameter
The proportioning of the liquid-crystal composition of table 5 embodiment 5 and performance perameter
The proportioning of the liquid-crystal composition of table 6 embodiment 6 and performance perameter
The proportioning of the liquid-crystal composition of table 7 embodiment 7 and performance perameter
In table 7, the synthetic route of compound 2-I d-16 is as follows:
Change starting raw material, can make equally other I compounds.
The proportioning of the liquid-crystal composition of table 8 embodiment 8 and performance perameter
The proportioning of the liquid-crystal composition of table 9 embodiment 9 and performance perameter
The proportioning of the liquid-crystal composition of table 10 embodiment 10 and performance perameter
The proportioning of the liquid-crystal composition of table 11 embodiment 11 and performance perameter
The proportioning of the liquid-crystal composition of table 12 embodiment 12 and performance perameter
The proportioning of the liquid-crystal composition of table 13 embodiment 13 and performance perameter
The proportioning of the liquid-crystal composition of table 14 embodiment 14 and performance perameter
The proportioning of the liquid-crystal composition of table 15 embodiment 15 and performance perameter
In table 15, the synthetic route of compound 3-I a-9 is as follows:
Change starting raw material, can make equally other I compounds.
Comparative example 1
The proportioning of the liquid-crystal composition of table 16 comparative example 1 and performance perameter
Comparative example 2
The proportioning of the liquid-crystal composition of table 17 comparative example 2 and performance perameter
Claims (10)
1. a liquid-crystal composition that can be used for various modes, is characterized in that, the component that comprises following weight percent:
The compound that (1) first component comprises formula I and general formula II representative, its content is 1-65%, preferably 35-65%;
(2) compound that second component comprises general formula III, general formula IV and general formula V representative, its content is 1-60%, preferably 30-60%;
The compound that (3) the 3rd components comprise general formula VI and general formula VII representative, its content is 1-55%, preferably 5-35%;
Wherein R
1, R
2, R
3independently represent separately H, methyl or C
2-C
12the alkyl or alkenyl of atom, the alkyl or alkenyl of described C2-C12 atom be unsubstituted, by CN or CF
3mono-substituted or mono-substituted by halogen, described C
2-C
12one or more CH in the alkyl or alkenyl of atom
2group can by-O-,-S-, ,-C ≡ C-,-CF
2o-,-OCF
2-,-OC-O-,-O-CO-with O atom not each other the mode of Direct Bonding replace;
L
1, L
2represent independently of one another H or F, L
3, L
4, L
5, L
6represent independently of one another H, F, Cl, CF
3, CHF
2in one;
Ring A and ring B independently represent separately
in one,
Ring C and ring D are from independently representing
in one,
Z
1represent singly-bound ,-CH
2cH
2-,
-CH=CH-,-C ≡ C-,-CF
2o-,-OCF
2-,-CH
2o-,-OCH
2-,-COO-,-OCO-,-C
2f
4-,-CF=CF-,-CH=CHCH
2one in O-,
Z
2represent singly-bound or-C
2h
4-,
Z
3and Z
4represent independently of one another singly-bound or
-CH
2o-,-C
2h
4-;
L, m, n, p, r and s represent 0 or 1 independently of one another;
Wherein, R
4, R
5, R
6and R
7represent independently of one another C
1-C
5alkyl or C
2-C
5thiazolinyl, wherein R
4, R
5in one or more-CH
2-can be replaced by-O-;
L
7, L
8, L
9, L
10and L
11represent independently of one another H atom or F atom;
X and Y represent F atom, OCF3, OCF independently of one another
2-CF=CF
2, OCHF
2and C
1-C
5alkyl in one;
Described general formula VI is one or more in five kinds of structures shown in formula VI A-VI E:
Wherein, R
8and R
9represent independently of one another C
1-C
5alkyl; L
12, L
13and L
14represent independently of one another H atom or F atom; W and Q independently represent F atom, OCF separately
3, OCF
2-CF=CF
2and C
1-C
5alkyl in one.
2. liquid-crystal composition according to claim 1, is characterized in that, the component that comprises following weight percent:
The compound that (1) first component comprises formula I and general formula II representative, its content is 35-65%, its formula of II compound >=5%;
(2) compound that second component comprises general formula III, general formula IV and general formula V representative, its content is 30-60%, its formula of III >=15%;
The compound that (3) the 3rd components comprise general formula VI and general formula VII representative, its content is 5-35%, its formula of VII≤15%.
3. liquid-crystal composition according to claim 2, is characterized in that, the component that comprises following weight percent:
The compound that (1) first component comprises formula I and general formula II representative, its content is 35-65%, its formula of II >=10%;
(2) compound that second component comprises general formula III, general formula IV and general formula V representative, its formula of III is 15-35%, and general formula IV is 5-20%, and general formula V is 5-20%;
The compound that (3) the 3rd components comprise general formula VI and general formula VII representative, its formula of VI is 6-20%, general formula VII is 0-15%.
4. according to the arbitrary described liquid-crystal composition of claim 1-3, it is characterized in that, described compound of Formula I is one or more in compound shown in following structure:
Described general formula II compound is one or more in compound shown in following structure:
4, liquid-crystal composition according to claim 1, is characterized in that, in general formula III, and R
4, R
5represent C
2-C
5alkyl, C
2-C
5thiazolinyl or C
1-C
5alkoxyl group, and wherein have one at least for alkyl.
5. according to the arbitrary described liquid-crystal composition of claim 1-4, it is characterized in that one or more in the following structure representative of the compound compound of general formula III representative:
6. according to the arbitrary described liquid-crystal composition of claim 1-4, it is characterized in that, the compound of described general formula I V representative is one or more in following structure representative compound:
7. according to the arbitrary described liquid-crystal composition of claim 1-4, it is characterized in that, the compound of described general formula V representative is one or more in compound described in following structure:
8. according to the arbitrary described liquid-crystal composition of claim 1-4, it is characterized in that one or more in the following structure representative of the compound compound of general formula VI representative:
9. according to the arbitrary described liquid-crystal composition of claim 1-4, it is characterized in that one or more in the following structure representative of the compound compound of described general formula VII representative:
10. the application of the arbitrary described liquid-crystal composition of claim 1-9 in shutter glasses, 3D and TN, STN, TN-TFT, OCB, IPS, PS-IPS, VA-IPS, FFS, PS-FFS and PS-VA-IPS mode display part.
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